IMPPAT Phytochemical information: 
Rauwolscine
Rauwolscine
Summary

SMILES: COC(=O)[C@@H]1[C@@H](O)CC[C@H]2[C@@H]1C[C@@H]1N(C2)CCc2c1[nH]c1c2cccc1
InChI: InChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15+,17+,18+,19+/m1/s1
InChIKey: BLGXFZZNTVWLAY-DIRVCLHFSA-N
DeepSMILES: COC=O)[C@@H][C@@H]O)CC[C@H][C@@H]6C[C@@H]NC6)CCcc6[nH]cc5cccc6
Scaffold Graph/Node/Bond level: c1ccc2c3c([nH]c2c1)C1CC2CCCCC2CN1CC3
Scaffold Graph/Node level: C1CCC2CN3CCC4C5CCCCC5NC4C3CC2C1
Scaffold Graph level: C1CCC2CC3C(CCC4C5CCCCC5CC34)CC2C1
Functional groups: COC(C)=O; CO; CN(C)C; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Yohimbine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Yohimbine-like alkaloids
Synonymous chemical names:
rauwolscine, alpha-yohimbine, alpha yohimbine (rauwolscine), Rauwolscine, α-yohimbine(rauwolscine), rauwolscine (alpha-yohimbine), α-yohimbine, α-yohimbine (rauwolsine)
External chemical identifiers:
CID:CID_643606; ChEMBL:CHEMBL10347; ChEBI:CHEBI:48562; ZINC:ZINC000003977785; FDASRS:T4LJ7LU45W; SureChEMBL:SCHEMBL244514; MolPort-002-513-616
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Rauwolscine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 354.45
Log P RDKit 2.65
Topological polar surface area (Å2) RDKit 65.56
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.24
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.57
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Rauwolscine
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.772957
Rauwolscine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.37
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes
Rauwolscine
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000727ENSG00000178394HTR1A3350ChEMBL, NPASS
TAR_EXP_001261ENSG00000100567PSMA35684ChEMBL
TAR_EXP_001267ENSG00000126067PSMB25690ChEMBL
TAR_EXP_001262ENSG00000041357PSMA45685ChEMBL
TAR_EXP_000773ENSG00000169083AR367NPASS
TAR_EXP_001260ENSG00000106588PSMA25683ChEMBL
TAR_EXP_001259ENSG00000129084PSMA15682ChEMBL
TAR_EXP_001273ENSG00000100804PSMB55693ChEMBL
TAR_EXP_001263ENSG00000143106PSMA55686ChEMBL
TAR_EXP_000249ENSG00000274286ADRA2B151ChEMBL, NPASS
TAR_EXP_000243ENSG00000150594ADRA2A150ChEMBL, NPASS
TAR_EXP_001472ENSG00000153253SCN3A6328ChEMBL, NPASS
TAR_EXP_001471ENSG00000136531SCN2A6326ChEMBL
TAR_EXP_001470ENSG00000144285SCN1A6323ChEMBL
TAR_EXP_001366ENSG00000117152RGS45999NPASS
TAR_EXP_001343ENSG00000114200BCHE590BindingDB
TAR_EXP_000236ENSG00000170214ADRA1B147ChEMBL, NPASS
TAR_EXP_000255ENSG00000184160ADRA2C152ChEMBL, NPASS
TAR_EXP_000233ENSG00000171873ADRA1D146BindingDB, ChEMBL, NPASS
TAR_EXP_000174ENSG00000222028PSMB11122706ChEMBL
TAR_EXP_001269ENSG00000277791PSMB35691ChEMBL
TAR_EXP_001266ENSG00000008018PSMB15689ChEMBL
TAR_EXP_001278ENSG00000205220PSMB105699ChEMBL
TAR_EXP_001277ENSG00000239836PSMB95698ChEMBL
TAR_EXP_001276ENSG00000235715PSMB85696ChEMBL
TAR_EXP_001275ENSG00000136930PSMB75695ChEMBL
TAR_EXP_001274ENSG00000142507PSMB65694ChEMBL
TAR_EXP_000223ENSG00000154611PSMA8143471ChEMBL
TAR_EXP_000433ENSG00000168496FEN12237NPASS
TAR_EXP_000239ENSG00000120907ADRA1A148BindingDB, ChEMBL, NPASS
TAR_EXP_001264ENSG00000100902PSMA65687ChEMBL
TAR_EXP_001265ENSG00000101182PSMA75688ChEMBL
TAR_EXP_001270ENSG00000159377PSMB45692ChEMBL